Deployment Strategist - Chicago

At Rec (rec.us) , we’re reimagining how the world plays, trains, competes, explores and gets outside. Our mission is to empower the entire recreation community to thrive, and our vision is bold: power recreation worldwide.

Booking a tennis court? Signing your kid up for swim lessons? Competing in a rec league? It shouldn’t feel like filing your taxes. We're partnering with parks & rec departments, golf courses, campgrounds, gyms and more to transform a $105B industry stuck in the Stone Age.

We’re not just putting recreation online—we’re redesigning it from the ground up, for the mobile-first, AI-powered world we live in.

And about AI? From simplifying registration flows to auto-scheduling entire recreation departments to empowering parks & rec staff to utilize the data to make their programming better, we use AI where it makes a real impact. We’re builders at heart, using the best tools to solve real problems for real communities.

If you get fired up by making tech that powers our communities— families, coaches, and kids all over the country—come join us.

We’re a small team with outsized ambition. We’ve built products and led teams at places like Google, Amazon, Uber Eats, MasterClass, The Athletic and more. Now we’re channeling all that energy into something fresh—and fun.

We care about how we build, not just what. Our culture is fast, focused, and full of pride. We keep our standards high, our egos low, and our Slack memes spicy.

• Be Relentless. Move fast. Own it. Ship real value early and often.

• Win Together. Speak up, go beyond the boundaries of your role. That's how we win.

• Take Pride. Treat this like it’s yours—because it is.

As a Customer Success Manager, you will be responsible for managing everything it takes to make each city partnership a success. This includes leading deployment engagements to launch new cities, developing deep relationships with city partners and acting as their voice internally, and building the processes needed to ensure existing city deployments thrive and grow into upsell opportunities.

This is a role for the client operations “athlete”, a voracious learner that wants exposure to all aspects of our B2B SaaS business and is relentlessly resourceful in achieving their goals. You should be client-obsessed and ready to build solutions to whatever challenge a city is facing. This is a strategic role and you'll have both the freedom and responsibility to become the domain expert trusted to make the right calls. However, this is also a hands-on early stage role where strategic insight comes from putting in the execution work yourself.

• Own city partnerships: Lead onboarding, ensure smooth deployments, and build trusted relationships with city leaders.

• Drive adoption & growth: Proactively identify opportunities to expand city partnerships and increase engagement with Rec.

• Be the voice of the customer: Share insights with product, sales, and engineering to improve our platform and processes.

• Build for scale: Create repeatable playbooks and processes that make every deployment faster and smoother.

• Lead cross-functional projects: Coordinate across teams to ensure each new city launch is a success.

• Deliver impact: Use data and insights to drive measurable improvements for both our customers and internal operations.

• 4+ years of experience in consulting or client-facing roles at high-growth startups

• Excellent at building and maintaining relationships with senior stakeholders

• Strong communicators — can clearly share insights and tailor solutions to client needs

• Strategic thinkers who can break down complex problems and execute solutions

• Highly organized and able to manage multiple projects at once

• Comfortable with data and analysis (Excel, SQL, or similar tools)

• Resourceful and entrepreneurial — you find ways to make things happen, even with limited resources

• Excited to build from 0→1 and scale a fast-growing SaaS company

• Compensation: $90,000–$130,000 base + meaningful equity (final offer will be based on your background, experience and skillset)

• Benefits: Flexible PTO, top-tier health/dental/vision, and a 401(k) plan to support your future.

Ready to build something real? Something fun? Something big?
We’re ready for you.